Dimethylamine → HCID 20508546, compound

HRID 1758785Notes

Reaction equation

HRID 1758785 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N:19]=[C:20]=[O:21])[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1.FC1C=CC=CC=1[C:33]1C2C=C(NC(NCCO)=O)C=CC=2N2C=NN=C2[CH2:35][N:34]=1.NC1C=CC2N3C(C)=NN=C3CN=C(C3C=CC=CC=3Cl)C=2C=1.C(=O)([O-])[O-].[Na+].[Na+].CNC>C(#N)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][C:20](=[O:21])[N:34]([CH3:35])[CH3:33])[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 125625156-(2-Chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-amineHCID 20508545HCID 20508545, compoundHCID 20508562HCID 20508562, compound

Product 1

HCID 20508546HCID 20508546, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [6-(o-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]isocyanate, prepared as described in paragraph (a) of Example 1 from 7.0 g (21.6 mmol) of 8-amino-6-(2-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine, but using methylene chloride in place of 1,2-dichloroethane, is treated while stirring and cooling with ice with a suspension of 8.7 g (81.9 mmol) of sodium carbonate in 50 ml of ice-cold methylene chloride and 5 g (111.1 mmol) of dimethylamine, the suspension being added in one portion. After the addition of 60 ml of dry acetonitrile, the mixture is stirred at room temperature for 20 hours and concentrated at 50° C. in vacuo. The residue is suspended in 100 ml of methylene chloride and 100 ml of water and filtered off. The material remaining is dissolved in 80 ml of hot ethanol and left to stand at -10° C. overnight. After filtering off the resulting crystals, there is obtained 3-[6-(o-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepin-8-yl]-1,1-dimethylurea of melting point 186° C. (decomposition).

Workup

  1. additionis treated
  2. additionthe suspension being added in one portion
  3. stirringthe mixture is stirred at room temperature for 20 hours
  4. concentrationconcentrated at 50° C. in vacuo
  5. filtration100 ml of water and filtered off
  6. dissolutionThe material remaining is dissolved in 80 ml of hot ethanol
  7. waitleft
  8. filtrationAfter filtering off the resulting crystals

Sources & evidence

ORD record
ord-aa114f090e7a4fc68f6a5cb7f31021ce
Source dataset
uspto-grants-1983_02
Patent number
US04374773

Reaction notes

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